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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
3-[(1R,3S,9S,11R,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
State
State

At room temperature, digoxin is in a solid state. It is typically stored at room temperature in a tightly sealed container, protected from light and moisture.

Melting point (Celsius)
249.00
Melting point (Kelvin)
522.15
Boiling point (Celsius)
150.00
Boiling point (Kelvin)
423.15
General information
Molecular weight
780.95g/mol
Molar mass
780.9450g/mol
Density
1.1000g/cm3
Appearence

Digoxin appears as a white to off-white crystalline powder. It is practically odorless and possesses a bitter taste. It is freely soluble in pyridine, slightly soluble in water and alcohol, and practically insoluble in chloroform and ether. Its crystalline nature is apparent under a microscope.

Comment on solubility

Solubility of 3-[(1R,3S,9S,11R,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

The solubility of the compound 3-[(1R,3S,9S,11R,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one can be assessed through various factors:

  • Polarity: The presence of multiple hydroxyl (-OH) groups suggests that the compound is likely polar, which may enhance solubility in polar solvents such as water.
  • Hydrogen Bonding: Due to its hydroxyl groups, this compound is capable of extensive hydrogen bonding with solvent molecules, potentially increasing solubility in aqueous solutions.
  • Structural Complexity: Its complex structure could also limit solubility; steric hindrance might impede solvation, particularly in nonpolar solvents.

As a general rule, the solubility of organic compounds can often be predicted by the “like dissolves like” principle, meaning polar compounds are more likely to dissolve in polar solvents. Therefore, despite the likelihood of significant solubility in aqueous environments, it is important to conduct experimental solubility tests to determine the precise behavior of this compound in different solvents.

Interesting facts

Interesting Facts about 3-[(1R,3S,9S,11R,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

This complex compound, often referred to as a natural product, belongs to a class of substances that are biologically significant due to their involvement in various metabolic pathways. Here are some fascinating aspects of this intricate molecule:

  • Natural Occurrence: This compound is found in various plants and has been used in traditional medicine for its beneficial properties.
  • Structural Complexity: With multiple hydroxyl groups and a fused ring system, its structure showcases the vast diversity in organic chemistry.
  • Biological Activity: Compounds like this often exhibit a range of pharmacological effects, including antioxidant and anti-inflammatory properties, making them of interest in drug development.
  • Research Potential: Scientists are actively studying this compound to uncover its mechanisms of action, which may lead to novel therapeutic agents.
  • Chemical Synthesis: The synthesis of such complex compounds presents significant challenges, often requiring sophisticated strategies and reagents.

As a chemistry student or researcher, understanding such compounds not only enhances knowledge of organic synthesis but also emphasizes the importance of natural products in modern pharmacology. The exploration of these molecules highlights the intricate connections between nature and scientific discovery.


In the words of famed chemist Robert H. Grubbs, "The beauty of chemistry lies in its complexity." This quote resonates profoundly when studying a compound like this, reminding us of the challenges and wonders that make chemistry a continually evolving field.